Pandora's Box
By Alaina Brooks
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It was the last of the year - December 1996. A company out of
central Texas had contracted me to do some training for their
employees the final days of December. I took the opportunity as a
great way to get away from the family after Christmas and to enjoy
some warm weather in Austin, Texas. It would be fun to spend new
Year's Eve as Alaina - I was looking forward to the day. When I
began the classes, I was surprised to meet one of my old roommates
from college. Tom had always been a great friend and we both
enjoyed getting to renew a friendship that had faded with time and
distance. He had just moved to Austin and was a new employee and
was comforted at finding out that there would be at least one person
he would know.
Dec 30th - The first night in town, Tom and I had a great time.
We went out for drinks and dinner, told old war stories and got caught
up on each others lives. He told me about his family, his recent
divorce and his late in life move in career choices. We had a blast
going out on the town, drinking and remembering what it was like
when we were both in college.
Dec 31st 3:00pm. - The last days seminar went great, I ended it a
bit early in the afternoon and could hardly wait to go back to my
hotel and begin my transformation into Alaina. Tom came up to me
and asked if I would want to go to the party planned by the company
- "Come on, it'll be a lot of fun - besides I don't know a soul, and I'd
feel like a real shit if I didn't go." I hated to say no, but I made up an
excuse that I would just as soon get to bed early and pack because
the next days drive was going to be long. He persisted and said, that
we probably would not stay out much beyond 1 or 2 and that it would
be fun. I knew it would be fun and the thought of walking around a
hotel dressed as Alaina on New Year's Eve was just too much fun to
ever pass up on. He gave me a hard time about "getting old" but
after awhile he gave up by telling me that I would be missing a great
party.
4:30pm. - I arrived at my hotel and began my transformation
with a hot bubble bath. The feel of the bubbles on smoothly shaved
legs always puts me in the mood to dress elegantly. I finished doing a
close shave and stepped out of the tub ready to slip into the persona
of Alaina. I began by applying my makeup and perfume to all the right
areas, and then I slid into some sheer black pantyhose. I tightened
up my corset once more before proceeding to put on my black lace bra
and matching black lace camisole and slip. I checked the position of
my breast forms and marveled at how realistic my figure and shape
was. I pulled out my black sequined party dress and slipped into it. It
was short, three inches above the knee with long sheer black sleeves
and a low neckline. At first I thought it might draw too much
attention, but my legs are my best attribute so I thought " What the
heck". I had just bought a trio of necklace, earrings and bracelet - all
real and all very expensive. The gold diamond necklace accentuated
the low neckline , and the long sheer sleeves gave an air of real
elegance while still looking just sexy enough. I reached around and
zipped my dress up while noticing in the mirror how well it clung to
my body in the right places. The matching gold bracelet and dangle
earrings finished off the trio. The set had been extremely expensive,
but the feel of real gold and diamonds made me feel incredibly
feminine. I slipped into some three inch black patent pumps. I
proceeded to attach my red nails (not too long ) and finished them off
with two very feminine rings on each hand. The final touch - a long
dark brown wig that hung down to my mid back - long straight and
extremely sexy.
7:00pm. I stood in awe at the beautiful woman who I saw in the
mirror before me. I had taken my time, and my makeup was perfect
The dress, the hair, and makeup made for a nice combination. I had no
doubt I could pass off anywhere tonight.
My plan was to walk around the hotel that night and to enjoy the
freedom of being able to walk around and not look out of place. The
hotel was buzzing with people and most of them were already
dressed formal and semiformal - this was going to be fun. A quick
cruise through the lobby, a trip up the elevator, and maybe a walk
outside - I was so excited I could hardly think straight. I had gone
out a couple of times before, but never on such a wild night
I packed a small black sequined purse with emergency makeup,
perfume, a brush and an extra set of nails (just in case),my cell
phone, some women's cigarettes, and my room key. With a deep sigh
of nervousness, I opened the room door and stepped out. People
were in the hall and I could feel that a group of older men watched
me as I stepped out into the hall. I held my head up high and casually
walked by them as I proceeded to the elevator. I could feel them
looking me over as I walked by. The feeling was fantastic. As I
reached the elevator, I suddenly realized that I had not packed any
money, so I turned around and returned to the room. When I passed
the men in the hall again, I heard one of them issue a low hushed "U-
mm-mm - she's nice looking!" This made me feel great to know that
I wasn't getting read.
Surprise
Back in the room, I packed in some cash just in
case I needed it. I checked over everything again and headed for the
door. I opened the door when I remembered that I would need my
lighter if I was going to smoke a cigarette, so with the door half open,
I walked back into the room and searched for the lighter I had bought
just for this occasion. I turned to head out the door and then to my
total horror - there stood Tom in the open door way of my room. I
freaked - I gasped and in an almost whisper I felt myself say "Oh shit
- Tom !!"
Bewildered he said "What? "
We stood there looking at each other for what seemed like an
eternity. He looked perplexed and stunned as he came to the
realization that this woman was ..... me . After a few seconds, he
said:
"Well, are you going to ask me in ?
A smile broke out on our faces and we both laughed as he stepped
into the room. From his look, I knew everything would be OK. We
talked for awhile and I explained that I was a crossdresser. I had
always been a crossdresser.
He was surprised to find out that while
we had been roommates in college, that competitive bicycling had
been a great excuse to justify keeping my legs shaved. When he and
our other roommates had gone home at times, I had a secret stash of
clothes I would put on. He never suspected , I did not seem to fill his
stereotype of what a crossdresser would be like. He told me that he
was aware of what crossdressers were and had been a bit curious,
but I had been the very first one he had ever met. He complimented
me and told me that if I had not called out his name, he would have
excused himself from the room and taken it for granted that a
mistake had been made - either he was in the wrong hotel room, or
that I had checked out.
"I would never in a million years suspected this was you" he said. "You're very convincing - you make a very beautiful woman"
I felt myself blush. I was so flattered by his compliment.
"I would never suspect you were anything other than a good looking
woman. I came by so sure that I could convince you to go to the party with
me."
I told him "I'm sorry to disappoint you - Now you know why I didn't
want to go out. "
I told him that I had planned to walk around the hotel and maybe
walk around a bit outside. With all the people partying in the hotel, I
probably would not be noticed.
"That's what you think !" he told me. "I'd lock on to you quick.
You're pretty fine looking. Alone, dressed to kill, with those killer legs - I'd have made the moves
on you right Now !"
I was sincerely flattered and also scared as I envisioned the
persistence of some unknown guy trying to pick me up. The thought
sent shivers up my spine - and I suddenly felt cold.
Tom was dressed nice. He was wearing a nice looking three piece suit
and looked like he was going to a formal party. He had planned to for
us to go and figured that if he came over, that I would not refuse. In
a soft and almost child like voice, he asked ..
"Well.... As long as your dressed for New Year's Eve, why don't we still
go to the party ?"
I immediately said "NO - no way - There will people there that I will
have instructed in the last three days - they'll know me !"
"Look" he said " I know you better than any of those people and if I
can't see you right now, what makes you think any of those people
will ?"
After a lot of convincing I half heartedly agreed. I felt very
confident about my looks, but I was unsure of my voice and we spent
a few minutes talking and practicing of my best female voice. After
some convincing, I agreed to go.
It would be a wild adventure. I had brought a coat just in case it was
cold - I grabbed it and we headed for the door.
We walked out the hotel side by side until we got to his car. I
was so impressed - he walked around to my side of the car and
opened the door for me. I sat down on the seat and then slid my legs
into the car. He closed the car door and walked around to the other
side. For a moment I felt a real tinge of panic - here I was dressed as
a woman - going to a corporate New year's Eve party - was I crazy ?
or what ? There would be people I had been teaching that day. Would
they recognize me? Would I be read ? My heart was pounding so
hard I almost got out of the car to run back to my hotel room. The
driver's side door opened and Tom got in. I told him of my fears and
he reassured me that if he could not recognize me, no one else would
either.
Thoughts of being in an auto accident filled my brain - visions of being
brought to a hospital dressed, made me feel cold.
"Quit that" I thought. "Enjoy yourself. It'll be alright" I pulled my
coat around me and decided that I was going to stop being paranoid
and enjoy the adventure.
Tom's car was new. He told me about it's new high performance
engine and how it was a treat for him after a messy divorce. The
plush leather seats were roomy and I began to feel very much like a
beautiful feminine lady. Along the way I spoke only as Alaina. I told
myself that I had to make sure that if I laughed or spoke that no
vestige of my male self could ever come out. Tom commented that I
did sound pretty convincing, but to be very careful not to slip up - the
voice could be a telltale if I did. I would have to concentrate - I
would have to be aware.
We arrived. The house was owned by the president of the
corporation, it was enormous. It oozed of rich society and opulence.
We walked up the long walk to the front of the house and I could hear
the live music coming from the rear. A cold shiver of anxiety went up
my spine but the clicking sound of my heels on the walkway made me
feel so wonderful, so feminine, that I began to calm down. I decided
I would relax, play the part and enjoy myself. When we got to the
front steps of the house, an older very elegant lady met us at the
door.
"Hi Tom" she said I'm so glad you could make it"
Tom introduced me as Alaina Brooks - I shock her hand gently and in
my best voice I said how glad I was to be here. I was afraid she
would ask where I was from and how Tom knew me - but she did not.
we walked into the main room of the house. The sound of my heels on
the smooth marble floors, and the feel of my dress moving as I
walked was almost intoxicating. I glanced to my right and saw
myself in a large full length mirror. It was a dream come true - I now
knew how Cinderella must have felt. Tom and I looked great
together. Without even being aware of myself, I took Tom's arm as
he escorted me into the main part of the house. I was pleased to
see that there were few people there and that It would not be
crowded. Tom laughed and told me to expect at least a hundred
people by midnight.
We mingled for awhile and Tom introduced me as
a good friend from his home town. We made small talk and I enjoyed
standing hanging on to Tom's arm while the men made small talk. I
had to bite my tongue many times as the male part of me wanted to
engage in conversion - instead, I enjoyed just adding comments once
in awhile.
After awhile Tom and I took the tour of the house -
incredible. The house must have been easily in the area of 5- 7000
feet in area. The artwork, the floors and the general decore of the
house talked volumes of a very successful company.
As the night wore
on, the band began to play again and people started to dance. By this
time we had had a few drinks and I was feeling a bit warm and fuzzy
and pretty good about being out. I had always wanted to dance so I
asked Tom if he would dance with me. He said sure, it would be fun.
we danced several songs and I know I really enjoyed moving to the
music especially being slightly intoxicated. We were in the middle of
the dance floor when the next song that began to play was a slow
song. I was unsure of what to do and I thought Tom would lead me
off the dance floor, but to my surprise, he slid his hand around my
waist and pulled me close to him. With one arm around my waist and
the other holding mine, we moved slowly to the music.
It was so
incredible to be held close as we swayed to the music. He led and I
followed as we moved with all the other couples on the dance floor.
We exchanged small talk and he again complimented me on how
beautiful I looked. We danced cheek to cheek and I could feel his
breath on my neck.
"You smell wonderful" he said. I now knew how
women felt when men complimented them. The dance ended and I so
wanted the band to play another slow song. We walked out of the
room and onto the rear deck of the house. The night was clear and
cloud free and it felt wonderful when Tom took my hand in his as we
walked around the well lit pool of the estate. I stopped and reached
into my purse for a cigarette and Tom lit it for me. We talked about
how I felt to be here. I told him this was the ultimate in any
experience I had ever had. I told him how wonderfully feminine I
felt, To dance, to be held and how wonderful it felt to have him hold
my hand and to escort me as if I were the beautiful woman I felt I
was.
He said "How ironic this all is." Here I am out on a date for the first
time in seventeen years - the first time since my divorce with Linda,
and I find myself out with a woman I cannot have - an illusion."
In a soft feminine voice I whispered "I'm sorry - maybe this was a bad
idea."
"Oh no , no, no," he said. "that's the thing that's so ironic."
I thought it would be almost like a college prank to escort you here - I thought it would be something we would both laugh at later - the
absurdity of it all..... I didn't expect myself to enjoy it so much."
"I feel almost guilty being here with you" he said.
I reiterated "I'm sorry Tom - I guess I should not have come"
I felt guilty and confused.... had I come on to him... was I playing the
woman to much ? Was he getting repulsed at the thought of being
out with a transvestite ?
I then asked Tom "Maybe we should leave and you can tell them I
had an early flight out tomorrow"
"You don't understand" he told me. "I don't want to leave - I want
to stay and dance and have a few more drinks and laugh. I haven't
had such a good time on a date in a long long time." We both laughed
as if we were kids that had been caught being naughty.
I told him "Thanks" "I don't mean to make you feel uncomfortable"
"Please let me know if I do."
We walked back into the house and we grabbed another drink.
Sipping on Gin and Tonics made me feel warm and fuzzy inside. The
slight wuzziness made the whole experience just that more exciting.
We finished our drinks and began to dance again and as luck would
have it, we hit another slow dance. I was so excited about being held
and slowly moving to the music that I had to contain my enthusiasm
when Tom asked me
"Alaina, would you like to dance this one ?'
Softly I replied "Yes, ...Please"
We moved slowly to the music. I enjoyed feeling Tom holding me
close to him. All of a sudden the music stopped. The countdown for
New Years was upon us. We stood on the dance floor still holding
each other as the countdown reached zero. Everyone shouted "Happy
New Year!"
At that moment, Tom faced me and kissed me. I had
always thought that I would never in a million years allow a guy to
kiss me. But I was caught off guard and when I felt his lips press
against mine I almost backed away - but instead - I felt myself
kissing him back. It was a gentle, romantic kiss. Our lips touching,
our mouths just barely open . It was not a deep kiss, but a very
loving kiss. We pulled apart and looked into each others eyes. I
think both of us were surprised that we had actually kissed. Maybe it
was the alcohol or maybe it was just a longing both of us wanted. We
both stared at each other in disbelief. Both his arms were still around
my waist and my arms were around his shoulders. I could tell it was
a first experience for both of us and we were both feeling anxiety.
We walked back to our table and ordered another drink. My head was
reeling - I could not believe I had let him kiss me.
We continued stayed at the party playing pool, dancing, drinking,
and generally having a great time until just after two in the morning.
Both of us were a bit drunk and I knew neither one of us should drive.
The owner insisted that we leave the car there and that she would
pick up the tab for cab fare (although it was free that night). Tom and
I walked to the awaiting cab and got into the back seat. We sat in the
back talking and laughing and enjoying ourselves . We talked about
all the things we had seen and done that night. I could not believe it -
I had actually pulled it off.
At one point while we were laughing, Tom
placed his hand on my leg just above the knee. I flinched a bit, but it
felt good to feel his hand on the smoothness of my hose - and I didn't
bother to object any. We arrived at the hotel and Tom and I walked
leisurely around the hotel laughing, talking and holding hands. We
arrived at my door and I stopped to reach into my purse for the room
card. I felt a scared excitement - I felt myself shaking with
nervousness. Was I crazy ? Deep down inside, I wanted so much to
be kissed again. I pulled the room card from my purse and then
looked at Tom. In a soft demure voice I said "I had a great time,
Tom. This is was a lot of fun. Thanks for taking me along"
"Thank you ! It was a lot of fun." he said.
"Thanks for everything Alaina" We looked at each other and our eyes
spoke volumes. With this, Tom slowly put his hands around my waist
and pulled me close to him. He looked into my eyes and, almost
instinctively, put my arms up on his shoulders and around his neck.
We looked at each other for what seemed like an eternity. Nothing
was said - we just stared into each others eyes - and I knew he knew
I wanted him to kiss me.
He pulled me close to him as he moved to
have his lips meet mine. I closed my eyes and our lips met and we
kissed a soft gentle kiss. We both pulled away just slightly as we
looked into each others eyes. I moved to him as I closed my eyes
again. The feel of his lips gently pressed against mine made the
feeling of being a woman so real. His kiss was gentle and very
subtle. The feel of his lips, the probing of his tongue was like nothing
I had ever imagined. We kissed gently at first and then deeply. His
hands moved slowly up and down the small of my back as our lips and
tongues embraced . He held me tightly against him. The smoothness
of my dress and hose, the tightness of my heels, the feeling of my long
hair on the nape of my neck while being held was an incredible
sensation. To feel him against me was an incredible high. I could feel
his excitement.
We broke from our embrace and we both went into the room. We
talked about the night's experience and how much fun we had had.
We talked of future plans to maybe get together - although I knew it
would never be arranged. We had an awkward moment of silence
where I think both of us felt a little unsure of what to do next. At
this point I stood up and Tom said goodbye and wished me well.
He left and I sat on the bed looking at myself in the mirror.
What had happened this night ? Had I crossed the line ? What were
my feelings on the whole thing ? I had enjoyed myself a thousand
times more than I had ever expected to. This had been a fantasy I
had only dreamed about for years. It was then and there that I came
to the realization that I had truly opened Pandora's box ... and things
would never be the same again.
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